No one can predict/time the market, and you don't want to be waiting on the sidelines indefinitely.

If I were to keep the home indefinitely, I feel like there is no real downside besides owing way too much on the home which obviously isn't a "good" situation but I think as long as you hold it as a rental, there is no real loss?

If that's the case, then that could take an indefinite amount of time.

@Steven Wetherill I would encourage you to proceed with caution but also understand that trying to time the market can leave on the sidelines indefinitely. 

And you can 1031 and indefinitely all depreciation recapture and the gain associated with the investment side.

You could be waiting an indefinite amount of time.

Inspector said its not something that would need immediate attention and could (*could*) be fine for years, if not indefinitely.

But the reward at the end can be pretty nice when you defer all that tax indefinitely.

I was set to close on my 2 flat last month but the closing has been push indefinitely because of the zoning certificate. 

By following the process they will indefinitely defer all tax on the gain from the sale.They have put a cooperation clause in the contract to give you notice that a 1031 is happening.